Operation Market Garden was the largest paratroop drop of the Second World War; It was also one of the worst operational failures. What strategy could have led the Allies to such an incredulous failure and what lessons can be learned for future military operations? Several timeless lessons are apparent from an analysis of the operation: (1) at the strategic level, military planners must never lose sight of the political reasons which fostered the initial conflict; (2) at the operational level, total coordination and planning with all elements of an operation remain critical to the successful execution of any plan; (3) logistics shortages caused the troops to be ill prepared; (4) most importantly, at the tactical level commanders must learn to "read the troops," watch their collective behavior and be ready to step in to keep them focused on the ultimate goal, the satisfactory completion of the mission; (5) from a leadership perspective, we learn that truly great leaders sacrifice their personal ambitions for the good of the unit effort and the successful execution of the mission.